An interesting proposal

[jessica_brink]

Hi everyone, I've been away for some time and haven't had the opportunity to come here but now I've finally and read all your messages and have already replied to certain posts or statements as you can see. Now, let me give you an update of what's happening.

Inspired by the - pretty much unanimous - advice to go for it, I've confirmed my friend I'll go with her dressed up as a girl. We did agree that we'll be trying on outfits in her room first before I go out like this to make sure I look somewhat convincing, that we'll keep this on the down low to other friends, AND that she's going to give me a little bit of training on female mannerisms during the try-out session.

The try-out will take place this Thursday, she's going to have some clothes laid out for me. I've no idea which ones exactly, but we did already decide that's I'm going to be wearing a dress. Like I mentioned in my OP she has two wigs so we'll try those on, and she already insisted I wear a bra and panties, so no need to worry about that anymore.

I can imagine many of you wanna see pictures. As of right now I can't say if I'll be confident enough to share pics of myself as a girl, but I'll definitely try to take pics of the clothes and wigs, so stay tuned for that.

Once again, thanks for the support, girls! If you're just tuning in, please continue to tell me your advice.

Jessica xxx

[ClosetED]

Glad to hear you are going for it. Since she does not know, you don't have to let on you have enjoyed this in the past. Let her do it all for you but you can encourage her to do all she wants simply because you see how much she enjoys this - you are just glad to make her happy. You can later admit you did enjoy this "first" experience and you would be willing to do it again for her. If someone questions you during the meeting, you can say you are doing this only because she asked you to and you support her 100% as well as general LGBT causes.
As to future relationship, maybe seeing you are able to be the best of both worlds, might open up possibilities. You can start letting her think she opened this new world to you, and later you can share your prior love.
Hugs, Ellen

[Becky Blue]

Great the hear Jessica you will have an amazing time, its such a perfect opportunity

...word of warning.. you will be hooked for life!!! I am very jealous of you as I think back to my first night out it was over 10 years ago and I can still remember every detail.

Best Advice I can give is - don't worry about passing, just try blend in and don't worry what strangers may think, Oh and take lots of pictures!!!

[Jessicajane]

absolutely go for it, ...you don't have to out yourself and can play the shy and embarrassed part..but if she asks you at the end of the night how you felt...be a little honest and tell her it was actually really good fun she might encourage it again..

[Glenda]

Glad you made your decision. Many years ago one of the girls on my APA 8-ball team invited me to dress and go to one of the lesbian bars that had recently opened. I went with her and her partner and two other straight girls from our bar. We had a great time and I still go out with all of them some twenty years later. Don't worry. It will be a blast.

[Lisalove1976]

I'm sure you will have a blast Jessica... I had a chance once that I turned down and regretted it for a LONG TIME.... make the most of it and have fun, you are not alone like most of us were/are so run with it.
as for pictures you should REALLY take some or have her take them on your phone that way you will have the only copies and you really shouldn't worry about posting them here as this community is GREAT and VERY supportive.

[Beverley Sims]

Go for it....
I did years ago and never looked back.
You are likely to get yourself a girlfriend or two also.
Not the one you are talking about, but, straight? ones..... :-)

[suzanne]

You have hit the motherlode in the friend girl department. Most of us in this forum can only dream of meeting a woman as supportive as your friend. I'm with everyone else who says "don't hesitate to go for it"

You say you're not really ready to be out? Why not let her believe she's the one who converted you to the joys of crossdresssing? Tell her you never imagined you could look and feel this wonderful. And it's probably not inaccurate either, because she will take you to a level of detail and sophistication that you haven't managed to do on your own.

Again, I say ENJOY!

[Janine cd]

I agree. This is a real opportunity to see yourself as a real woman.

[Jessica May]

Hey Jessica,
I'm glad you are getting the chance to try this and experience it in a setting with a friend. It really can be incredible . My first time going out was with the help of friends and I was truly lucky to get to enjoy the experience fully with them. I hope you have a great time trying on things today! and don't feel pressured to post photos dressed. Take things at your own pace as you feel comfortable. Each little step leads to something new. I hope this turns out to be a great experience for you.

All the best,
Jess

[Stephanie Nicole]

I guess I am a little too late to comment but it seems your on the right track with letting her dress you and teach you mannerisms to help pass. But my concerns are ( from my own college experiences thought I did not dress then) (a) College dorms are very busy places and if you are not out yet nut people there know you (and I'm sure they probably do) no matter how convincing you are, chances are high that someone will recognize you, (b) I don't know where on campus the meeting will take place bit you will at some point be walking across campus to the meeting or to a vehicle to get to the meeting and again that means crossing paths with other students.
I know when I attended college even though I didn't know I personally didn't know people it seemed like everyone was a friend of a friend so when something did occur it spread like wildfire across campus and eventually everyone knew about and in a relatively short time.
So my suggestion is to let her dress you up and practice the mannerisms and after that if you are comfortable with the risks then I say go for it, but if you even have a shred of concern that you will be found out and you think the risk and repercussions will be too high then I would say not to do it. I'm sure that is not the answer you were looking for but hers and your safety needs to be of paramount concern.

[5150 Girl]

Remember, this is a GBLT event! You will be among friends/ others in the or similar boat as you!
Also, you mentioned have some things of your own... I'd bring them to the try on session as well.

[ShelbyDawn]

I can't tell you what the best answer for your will be but I will say this; If I'd had that opportunity at your age, I wold have jumped all over it and at nearly 60, I have more regrets about things I never tried than things I tried that failed(and some abysmally)

[Sarasometimes]

You call yourself a closeted crossdresser but in 2015 you posted about how you arranged to spend 2 weeks living as 'housewife' with a man you met 6 month earlier? We never heard how that worked out?
After the housewife experience why would you need to ask us how to act like a girl? Bye

[jessica_brink]

I guess I am a little too late to comment but it seems your on the right track with letting her dress you and teach you mannerisms to help pass. But my concerns are ( from my own college experiences thought I did not dress then) (a) College dorms are very busy places and if you are not out yet nut people there know you (and I'm sure they probably do) no matter how convincing you are, chances are high that someone will recognize you, (b) I don't know where on campus the meeting will take place bit you will at some point be walking across campus to the meeting or to a vehicle to get to the meeting and again that means crossing paths with other students.
I know when I attended college even though I didn't know I personally didn't know people it seemed like everyone was a friend of a friend so when something did occur it spread like wildfire across campus and eventually everyone knew about and in a relatively short time.
So my suggestion is to let her dress you up and practice the mannerisms and after that if you are comfortable with the risks then I say go for it, but if you even have a shred of concern that you will be found out and you think the risk and repercussions will be too high then I would say not to do it. I'm sure that is not the answer you were looking for but hers and your safety needs to be of paramount concern.

I live in Belgium, here college and campuses are different from the US. It's basically just a house where a couple of people live together. Also it's not a meeting, just a LGBT bar. Also, should someone see me, I can simply say it's to support my friend, not to be taken too seriously.

[joank]

and what happened? The try on take place?

[jessica_brink]

Ok girls, this is what happened at the try-out. I went to her place, nervous as hell but also really excited. She had laid out some clothes already which got me reaally excited. First the make-up, nothing too much, just some lipstick, blush and mascara. Then we tried on two blonde wigs. I went for the longer of the two. Then I changed into a pair of panties and a bran she didn't mind. We filled the bra with water balloons. My breasts were quite big but then again she's quite busty as well, and I loved having them. Finally, we tried on several dresses until we decided to go for a long black one. Now I have to say, it felt sooo good showing off! I twirled around A LOT, feeling a bit like a princess. I also felt like I could be that person with her. Then she got me in some high heels and she taught me how to walk feminine (hands on hips),
which actually wasn't that bad. I also learned how to sit properly like a girl and then to practice my voice we pretended to be calling each other on the phone, like giggling girls talking about girl stuff. Overall it was a wonderful experience and I can't wait for us to go out actually. It took me some time to come down that's why I dodn't immediately post this. I didn't hesitate too much and my feminine behavior came quite naturally once I dressed up like a lady (apparently I'm quite girly for a girl and a bit of a bitch even at times haha). Now I didn't take any pics of myself, still not sure about that, but I did quickly take pics of the two wigs (I went for the long one as I said) and her panty drawer (I wore the pink one in the top right corner) just to give you girls something. I'll make a pic of the dress later, promise. Thanks again all of you for your kinds words of support.
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[nvlady]

You realize of course that now you must either come out to her, or at a minimum tell her you really enjoyed the experience and would like to do it again.

[Connie.Marie]

Jessica,
Congrats on getting dressed and being seen by your friend! I'm sure it was quite a rush.
So glad that it feels wonderful for you. It's great when you have a GG that helps.

Pics of the event would be nice. BTW, when is it?

Just a few suggestions,
borrow a purse (and keep track of it), take a pair of flats in your purse to change into when your feet need a break.
Take the water balloons down a notch from quite big to just big :-).
Pay attention to how she does your makeup. Ask questions to learn how to do it yourself. If a good opportunity comes up before the event, ask her to help you find the right shades of foundation & eye shadow for you.
Relax & Have fun.


NVLady,
No need for her to "come out".
Her friend saw Jessica's reaction so she already knows.

Hugs, Connie

[Sometimes Steffi]

So, let's be honest. You just won the lottery, and you almost didn't even buy the lottery ticket.

Your reactions, nervousness and excitement at the beginning, exhilaration in the middle, and a high so high that you didn't come down for days is very similar to what I felt my first time out of the house.

I hope there is much more to come. This girl may be hiding a deep dark secret from you. She may be Bi, and/or she might have enjoyed dressing you up as much or more than you enjoyed being dressed up. Somehow, things lined up almost too perfectly in that you are the same size in clothes and shoes, and she had wigs for you to put on.

[Territx]

I agree with others, (1) you did win the lottery and (2) you at least need to tell her that you enjoyed it/had a good time. Other than that, enjoy and relish every minute because these opportunities do not come around often, if at all, and if/when they do they pass so very quickly.

[deebra]

You could practice at home before going out, good excuse to get into bra, panties and heels and makeup. If you wanted to push the experiment to let her know you like the idea of dressing as a girl then you could ask her to borrow the clothing so you could practice at home. Would this put the CD thought in her head that you like to dress female, absolutely and this may not be a bad thing. Your previous thread said she insisted you wear a bra and panties. Sounds like she likes you in bra, panties, girl clothes. Yes you won the lottery.

[macada10]

And how were her reactions? Did she asked you to repeat? Did she flirt or you were acting as a couple?

[5150 Girl]

A word of caution.... For the day of the event, I would find an alternative to water balloons as they tend to pop rather easily!

[jessica_brink]

You could practice at home before going out, good excuse to get into bra, panties and heels and makeup. If you wanted to push the experiment to let her know you like the idea of dressing as a girl then you could ask her to borrow the clothing so you could practice at home. Would this put the CD thought in her head that you like to dress female, absolutely and this may not be a bad thing. Your previous thread said she insisted you wear a bra and panties. Sounds like she likes you in bra, panties, girl clothes. Yes you won the lottery.

Yes she's going to lend out the clothes to me to practice actually. Don't have them yet, probably gonna pick them up tomorrow! Reason she made me wear the bra and panties was to give me a feminine shape as well as making me feel more like a girl.

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And how were her reactions? Did she asked you to repeat? Did she flirt or you were acting as a couple?

Like I said we pretended to be girlfriends, chatting over girl stuff, not really as a couple.

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A word of caution.... For the day of the event, I would find an alternative to water balloons as they tend to pop rather easily!

Not sure what we could use as alternative. She might have had some wigs laying around at home but I'm pretty sure no breast forms. Water balloons do feel really nice though,, and it's easy to fill the bra with them (D cup)